Triethylamine → 6-((2R,5S)-2,5-Dimethyl-piperazin-1-yl)-nicotinonitrile

HRID 42175

Reaction equation

HRID 42175 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][NH:3]1.Cl[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=1.C(N(CC)CC)C>CN1CCCC1=O>[CH3:1][C@@H:2]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4][N:3]1[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2206722,5-Dimethylpiperazine, trans-HCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 574716106-((2R,5S)-2,5-Dimethyl-piperazin-1-yl)-nicotinonitrileYield 9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine (2S,5R)-2,5-dimethyl-piperazine (200 mg, 1.75 mmol), 6-chloro-nicotinonitrile (1.75 mmol) and triethylamine (5.25 mmol) in a 0.875 M solution of 1-methyl-2-pyrrolidinone. Microwave reaction mixture for 30 min at 150° C. Partition between ethyl acetate and water, collecting organic phase. Wash aqueous layer again with ethyl acetate and combine organics. Dry with sodium sulfate, filter and concentrate. Purify on preparative HPLC to give the title compound. (9% yield)

Workup

  1. customMicrowave reaction mixture for 30 min at 150° C
  2. customPartition between ethyl acetate and water
  3. customcollecting organic phase
  4. dry with materialDry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on preparative HPLC

Sources & evidence

ORD record
ord-bc5f400ac57641de862139b65cf0bb17
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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